4-(3'-methoxybenzylidene)-2-methyl-4-oxazolone | 41888-64-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(3'-methoxybenzylidene)-2-methyl-4-oxazolone
• 英文别名: (Z)-2-methyl-4-(3-methoxybenzylidene)-5(4H)-oxazolone；4-(3-methoxybenzylidene)-2-methyloxazol-5-one；(Z)-4-(3-methoxybenzylidene)-2-methyloxazol-5(4H)-one；4-(3-methoxy-benzylidene)-2-methyl-4H-oxazol-5-one；4-(3-Methoxy-benzyliden)-2-methyl-4H-oxazol-5-on；(E)-4-(3-methoxybenzylidene)-2-methyloxazol-5(4H)-one；(4Z)-4-[(3-methoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one
• CAS: 41888-64-6
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: PWPKCQPPIDXVNX-XFFZJAGNSA-N

物化性质

• 熔点：
  123-124 °C
• 沸点：
  337.2±52.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3'-methoxybenzylidene)-2-methyl-4-oxazolone 在 盐酸 、 sodium hydroxide 作用下， 生成 3-(3-Methoxyphenyl)-2-oxopropansaeure
  参考文献：
  名称：

  Potent, Selective Tetrahydro-β-carboline Antagonists of the Serotonin 2B (5HT_2B) Contractile Receptor in the Rat Stomach Fundus

  摘要：

  A series of potent, selective 5HT(2B) receptor antagonists has been identified based upon yohimbine, with SAR studies resulting in a 1000-fold increase in 5HT(2B) receptor affinity relative to the starting structure (-log K(B)s > 10.0 have been obtained). These high-affinity tetrahydro-beta-carboline antagonists are able to discriminate among the 5HT(2) family of serotonin receptors, with members of the series showing selectivities of more than 100-fold versus both the 5HT(2A) and 5HT(2C) receptors based upon radioligand binding and functional assays. As the first compounds reported with such selectivity and enhanced receptor affinity, these tetrahydro-beta-carboline antagonists are useful tools for elucidating the role of serotonin acting at the 5HT(2B) receptor in normal and disease physiology.

  DOI：

  10.1021/jm960062t
• 作为产物：
  描述：

  3-甲氧基苯甲醛 、 N-乙酰甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 生成 4-(3'-methoxybenzylidene)-2-methyl-4-oxazolone
  参考文献：
  名称：

  Atropos仅手性2,2'取代基的手性联苯双膦配体及其在Rh催化不对称加氢中的应用

  摘要：

  使用大体积的手性叔丁基甲基膦基嵌段，合理地设计并轻松合成了仅带有2,2'取代基的atropos手性联苯双膦配体。计算结果表明两种非对映异构体之间的自由能（7.8 kcal / mol）和从一种非对映异构体到另一种非对映异构体（27.7 kcal / mol和反向的19.9 kcal / mol）可获得的旋转能垒之间存在很大差异。该配体避免了制备轴向手性配体通常所需的费时的光学拆分，并且在Rh催化的不对称氢化反应中具有高反应活性和对映选择性。

  DOI：

  10.1002/adsc.201701281

文献信息

• Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C–H Bonds
  作者：Kyle Clagg、Haiyun Hou、Adam B. Weinstein、David Russell、Shannon S. Stahl、Stefan G. Koenig

  DOI：10.1021/acs.orglett.6b01592

  日期：2016.8.5

  A direct oxidative C–H amination affording 1-acetyl indolecarboxylates starting from 2-acetamido-3-arylacrylates has been achieved. Indole-2-carboxylates can be targeted with a straightforward deacetylation of the initial reaction products. The C–H amination reaction is carried out using a catalytic Pd(II) source with oxygen as the terminal oxidant. The scope and application of this chemistry is demonstrated

  已经实现了从 2-乙酰氨基-3-芳基丙烯酸酯开始直接氧化 C-H 胺化，得到 1-乙酰基吲哚甲酸酯。通过对初始反应产物进行直接脱乙酰化，可以靶向 2-吲哚羧酸酯。 C-H 胺化反应是使用催化 Pd(II) 源和氧气作为末端氧化剂进行的。这种化学的范围和应用已被证明对于许多富电子和贫电子底物具有良好到高的产率。所选产物通过铃木芳基化和脱乙酰化进行进一步反应，获得高度功能化的吲哚结构。
• Synthesis of new simplified hemiasterlin derivatives with α,β-unsaturated carbonyl moiety
  作者：Chinh Pham The、Tuyet Anh Dang Thi、Thi Phuong Hoang、Quoc Anh Ngo、Duy Tien Doan、Thu Ha Nguyen Thi、Tham Pham Thi、Thu Ha Vu Thi、M. Jean、P. van de Weghe、Tuyen Nguyen Van

  DOI：10.1016/j.bmcl.2014.03.091

  日期：2014.5

  In this Letter, we report a convenient and efficient method for the synthesis of new simplified derivatives of hemiasterlin in which the α,α-dimethylbenzylic moiety A is replaced by α,β-unsaturated aryl groups as Michael acceptor. Most of these derivatives have a strong cytotoxic activity on three human tumor cell lines (KB, Hep-G2 and MCF7). Analogs 17b and 17f showed a high cytotoxicity against KB

  在这封信中，我们报告了一种方便而有效的方法，用于合成半精胺素的新的简化衍生物，其中α，α-二甲基苄基部分A被α，β-不饱和芳基取代为Michael受体。这些衍生物大多数对三种人类肿瘤细胞系（KB，Hep-G 2和MCF 7）具有很强的细胞毒活性。类似物17b和17f显示出与紫杉醇和玫瑰树碱相当的对KB和Hep-G 2癌细胞系的高细胞毒性。
• Maekawa, Kei; Kajiwara, Hiroo; Iseya, Yoshiyuki, Heterocycles, 2003, vol. 60, # 3, p. 637 - 654
  作者：Maekawa, Kei、Kajiwara, Hiroo、Iseya, Yoshiyuki、Igarashi, Tetsutaro、Sakurai, Tadamitsu

  DOI：——

  日期：——
• The Meta<i>-</i>Green Fluorescent Protein Chromophore
  作者：Jian Dong、Kyril M. Solntsev、Olivier Poizat、Laren M. Tolbert

  DOI：10.1021/ja073622u

  日期：2007.8.1

  m-Hydroxy isomer of the green fluorescent protein synthetic analogue (m-HBDI) was synthesized. By analogy to hydroxystilbenes, longer singlet lifetimes and lower isomerization quantum yields were observed for the meta versus para isomer of the chromophore.
• Desai; Bhatt; Shah, Il Farmaco, 1996, vol. 51, # 5, p. 361 - 366
  作者：Desai、Bhatt、Shah、Undavia、Trivedi、Narayanan

  DOI：——

  日期：——